I search a bit for how to do this and it seems like Plex will display thumbnails in landscape mode if you set the agent to Personal Media. It’s currently set up like so and plex still display thumbnails in portrait mode. What else can I try?
Use a different client than Plex Web.
Pretty much any other Plex client will indeed show you landscape ‘posters’ in a Home video library.
The iOS client display them in landscape mode indeed (but not the AppleTv one, annoyingly). Is there really no way to get the configure the web interface to get landscape thumbnails?